CA2732947A1 - Process for preparing amines from alcohols and ammonia - Google Patents

Process for preparing amines from alcohols and ammonia Download PDF

Info

Publication number
CA2732947A1
CA2732947A1 CA2732947A CA2732947A CA2732947A1 CA 2732947 A1 CA2732947 A1 CA 2732947A1 CA 2732947 A CA2732947 A CA 2732947A CA 2732947 A CA2732947 A CA 2732947A CA 2732947 A1 CA2732947 A1 CA 2732947A1
Authority
CA
Canada
Prior art keywords
represented
formula
moiety
ruthenium catalyst
heteroaryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA2732947A
Other languages
English (en)
French (fr)
Inventor
David Milstein
Chidambaram Gunanathan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yeda Research and Development Co Ltd
Original Assignee
Yeda Research and Development Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yeda Research and Development Co Ltd filed Critical Yeda Research and Development Co Ltd
Publication of CA2732947A1 publication Critical patent/CA2732947A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/64—Acridine or hydrogenated acridine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
CA2732947A 2008-08-10 2009-08-10 Process for preparing amines from alcohols and ammonia Abandoned CA2732947A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US8770808P 2008-08-10 2008-08-10
US61/087,708 2008-08-10
PCT/IL2009/000778 WO2010018570A1 (en) 2008-08-10 2009-08-10 Process for preparing amines from alcohols and ammonia

Publications (1)

Publication Number Publication Date
CA2732947A1 true CA2732947A1 (en) 2010-02-18

Family

ID=41259988

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2732947A Abandoned CA2732947A1 (en) 2008-08-10 2009-08-10 Process for preparing amines from alcohols and ammonia

Country Status (7)

Country Link
US (3) US8586742B2 (enExample)
EP (1) EP2307431B1 (enExample)
JP (1) JP5738185B2 (enExample)
CN (1) CN102203108B (enExample)
AU (1) AU2009280778B2 (enExample)
CA (1) CA2732947A1 (enExample)
WO (1) WO2010018570A1 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004005108A1 (de) 2004-02-02 2005-10-27 Basf Ag Verfahren zur Herstellung von Polyisobutenylphenolen
WO2012052996A2 (en) 2010-10-19 2012-04-26 Yeda Research And Development Co. Ltd. Novel ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof
DE102011004465A1 (de) * 2010-09-10 2012-03-15 Evonik Degussa Gmbh Verfahren zur direkten Aminierung sekundärer Alkohole mit Ammoniak zu primären Aminen
DE102011075162A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur homogen-katalysierte, hochselektiven direkten Aminierung von primären Alkoholen mit Ammoniak zu primären Aminen bei hohem Volumenverhältnis von Flüssig- zu Gasphase und/oder hohen Drücken
DE102011003595B4 (de) 2011-02-03 2014-04-17 Evonik Degussa Gmbh Herstellung von in ihrer Hauptkette linearen primären Diaminen für Polyamidsynthesen
WO2012113475A1 (de) 2011-02-21 2012-08-30 Evonik Degussa Gmbh Verfahren zur direkten aminierung von alkoholen mit ammoniak zu primären aminen mittels eines xantphos katalysatorsystems
US8785693B2 (en) 2011-03-08 2014-07-22 Basf Se Process for the preparation of primary amines by homogeneously catalyzed alcohol amination
HUE025480T2 (en) 2011-03-08 2016-02-29 Basf Se Process for the preparation of di, tri and polyamines by homogeneous catalyzed alcohol amination
RU2013144823A (ru) * 2011-03-08 2015-04-20 Басф Се Способ получения алканоламинов путем гомогенного каталитического аминирования спиртов
US8912361B2 (en) 2011-03-08 2014-12-16 Basf Se Process for preparing di-, tri- and polyamines by homogeneously catalyzed alcohol amination
CN103502212B (zh) * 2011-03-08 2016-05-18 巴斯夫欧洲公司 制备通过均相催化醇胺化获得的伯胺的方法
AU2012224721A1 (en) * 2011-03-08 2013-10-03 Basf Se Method for producing primary amines by means of homogeneously-catalysed alcohol amination
US8637709B2 (en) 2011-03-08 2014-01-28 Basf Se Process for the preparation of primary amines by homogeneously catalyzed alcohol amination
US9193666B2 (en) * 2011-03-08 2015-11-24 Basf Se Process for preparing alkanolamines by homogeneously catalyzed alcohol amination
WO2012154945A2 (en) * 2011-05-11 2012-11-15 University Of Florida Research Foundation, Inc. Ono pincer ligands and ono pincer ligand comprising metal complexes
EP2875027B1 (de) * 2012-07-23 2018-05-02 Basf Se Verfahren zur homogen-katalysierten aminierung von alkoholen mit ammoniak in gegenwart eines komplexkatalysators ohne anionische liganden
US8853400B2 (en) * 2012-07-23 2014-10-07 Basf Se Process for the homogeneously catalyzed amination of alcohols with ammonia in the presence of a complex catalyst which comprises no anionic ligands
CN103626995A (zh) * 2012-08-21 2014-03-12 杜邦公司 由二醇和二胺制备聚酰胺的方法
EP3057935B1 (en) * 2013-10-15 2018-12-26 Rhodia Operations Process for forming primary, secondary or tertiary amine via direct amination reaction
WO2015109452A1 (en) * 2014-01-22 2015-07-30 Rhodia Operations Catalyzed amination of alcohols in aqueous medium
IL234478A0 (en) 2014-09-04 2014-12-02 Yeda Res & Dev Ruthenium complexes and their use for the preparation and/or hydrogenation of esters, amides and their derivatives
IL234479A0 (en) 2014-09-04 2014-12-02 Yeda Res & Dev A liquid hydrogen storage system based on a catalytic process for the preparation and hydrogenation of a cyclic peptide from 2-aminoethanol and 2-(methylamino)ethanol
WO2016074121A1 (en) * 2014-11-10 2016-05-19 Rhodia Operations Process for forming amine by direct amination reaction
CN104804048B (zh) * 2015-05-25 2017-09-22 洛阳师范学院 N‑取代苄基氨基膦钳型环钌双膦化合物及其制备方法和应用
DE102015217088B4 (de) * 2015-09-07 2021-01-21 Volkswagen Aktiengesellschaft Verfahren zur Herstellung eines Halbzeugs aus einem polyamidhaltigen Verbundwerkstoff und daraus erhaltenes Halbzeug
CN107778182B (zh) * 2016-08-29 2020-06-02 南京理工大学 一种合成n-烷基芳胺的方法
US10774035B2 (en) 2016-09-23 2020-09-15 Umicore Ag & Co. Kg Preparation of amino acids and amino acid derivatives
CN107245066B (zh) * 2017-06-26 2019-10-18 浙江大学 一种选择性制备糠胺或四氢糠胺的方法
MX2024004406A (es) * 2021-10-12 2024-05-02 Huntsman Petrochemical Llc Metodo de produccion de aminas de eter alcoxiladas y usos de las mismas.
CN114805259B (zh) * 2022-05-09 2024-01-12 厦门大学 一种耐失活镍基催化剂上糠醇选择性胺化制备糠胺的方法
JP2023177660A (ja) * 2022-06-02 2023-12-14 旭化成株式会社 ルテニウム錯体の製造方法、並びにルテニウム錯体及びこれを用いたジアミンの製造方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5912106B2 (ja) * 1979-02-21 1984-03-21 花王株式会社 脂肪族アミンの製造方法
DE19652350A1 (de) * 1996-12-17 1998-06-18 Studiengesellschaft Kohle Mbh Neue Katalysatoren aus Übergangsmetallverbindungen und 4,5-Diphosphinoacridin-Liganden
WO2007104359A1 (en) 2006-03-14 2007-09-20 Jacobs University Bremen Ggmbh Synthesis of amines with ytterbium lewis acids
WO2007104357A1 (en) 2006-03-14 2007-09-20 Jacobs University Bremen Ggmbh Synthesis of amines with catalytic amounts of mild lewis acids
US8178723B2 (en) * 2007-10-30 2012-05-15 Yeda Research And Development Co. Ltd. Process for preparing amides from alcohols and amines

Also Published As

Publication number Publication date
US8889865B2 (en) 2014-11-18
US20110152525A1 (en) 2011-06-23
CN102203108A (zh) 2011-09-28
EP2307431A1 (en) 2011-04-13
JP5738185B2 (ja) 2015-06-17
HK1159114A1 (en) 2012-07-27
AU2009280778B2 (en) 2013-07-25
JP2011530408A (ja) 2011-12-22
AU2009280778A1 (en) 2010-02-18
US20140288306A1 (en) 2014-09-25
US8586742B2 (en) 2013-11-19
US20140046065A1 (en) 2014-02-13
CN102203108B (zh) 2014-10-22
US8779136B2 (en) 2014-07-15
WO2010018570A1 (en) 2010-02-18
EP2307431B1 (en) 2012-12-26

Similar Documents

Publication Publication Date Title
AU2009280778B2 (en) Process for preparing amines from alcohols and ammonia
EP2629889B1 (en) Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof
US20070073055A1 (en) Transition metal complexes of N-heterocyclic carbenes, method of preparation and use in transition metal catalyzed organic transformations
CN114080379B (zh) 在Ru-PNN配合物存在下将酯类氢化为醇类
CN113845550B (zh) 一种含有卤代苯环的柔性大位阻n-杂环卡宾钯配合物和制备方法及其应用
Lu et al. Asymmetric Henry reaction catalyzed by Cu (II)-based chiral amino alcohol complexes with C2-symmetry
Çiçek et al. Half-sandwich Ru (II) arene complexes bearing benzimidazole ligands for the N-alkylation reaction of aniline with alcohols in a solvent-free medium
HUE027438T2 (en) A method for preparing primary amines by homogenous catalyzed alcohol amination
US20100099875A1 (en) New ortho-functionalized p-chiral arylphosphines and derivatives: their preparation and use in asymmetric catalysis
CN110156832A (zh) 双缩醛基苯基膦、它们的制备方法及在偶联反应中的用途
Šebesta et al. Influence of structural changes in ferrocene phosphane aminophosphane ligands on their catalytic activity
Hong et al. Highly efficient and well-defined phosphinous acid-ligated Pd (II) precatalysts for Hirao cross-coupling reaction
US8394979B2 (en) Process for preparing cycloplatinated platinum complexes, platinum complexes prepared by this process and the use thereof
CA2556850A1 (en) Transition metal complexes of n-heterocyclic carbenes, method of preparation and use in transition metal catalyzed organic transformations
WO2015039606A1 (en) Novel phosphines, synthesis thereof and their use in catalysis
HK1159114B (en) Process for preparing amines from alcohols and ammonia
US9340519B2 (en) Paracyclophane-based ligands, their preparation and use in catalysis
JPH01153660A (ja) アリル型アミンの製造法
CN119822988A (zh) 一种甲酰苯胺类化合物的光化学合成方法
Xia et al. Construction of Novel Chiral NPN Ligands and the Application in Gold (I)‐Catalyzed Asymmetric Cycloaddition Reactions
CN120698854A (zh) 一种多取代烯丙醇类化合物的合成方法
CA2551412A1 (en) Transition metal complexes of n-heterocyclic carbenes, method of preparation and use in transition metal catalyzed organic transformations
CN119899195A (zh) 一种不对称光催化螺环化构建手性螺环胺的方法
CN121085785A (zh) 手性膦氮氮三齿配体在不对称烯丙基取代反应中的应用
CN120987716A (zh) 一种轴手性烯丙基胺类化合物的制备方法

Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20140812